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Volume 66 
Part 1 
Pages o221-o222  
January 2010  

Received 24 November 2009
Accepted 15 December 2009
Online 24 December 2009

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.005 Å
R = 0.053
wR = 0.175
Data-to-parameter ratio = 17.6
Details
Open access

2-[3-(Methyldiphenylsilyl)propyl]isoindoline-1,3-dione

aDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, Wisconsin 53706, USA
Correspondence e-mail: iguzei@chem.wisc.edu

In the title compound, C24H23NO2Si, the dihedral angle between the planes of the phenyl rings attached to the Si atom is 80.78 (10)°. In the crystal, the molecules form sheets lying perpendicular to [101] via C-H...O interactions. These sheets are stacked and linked in a three-dimensional framework by additional C-H...O interactions in the [10[\overline{1}]] direction.

Related literature

For literature related to drug design see: Bains & Tacke (2003[Bains, W. & Tacke, R. (2003). Curr. Opin. Drug Discov. Devel. 6, 526-543.]); Gately & West (2007[Gately, S. & West, R. (2007). Drug Dev. Res. 68, 156-163.]); Guzei et al. (2010a[Guzei, I. A., Spencer, L. C. & Zakai, U. I. (2010a). Acta Cryst. E66, o219-o220.],b[Guzei, I. A., Spencer, L. C. & Zakai, U. I. (2010b). Acta Cryst. E66, o223-o224.]); Lee et al. (1996[Lee, Y. J., Ling, R., Mariano, P. S., Yoon, U. C., Kim, D. U. & Oh, S. W. (1996). J. Org. Chem. 61, 3304-3314.]); Tsuge et al. (1985[Tsuge, O., Tanaka, J. & Kanemasa, S. (1985). Bull. Chem. Soc. Jpn, 58, 1991-1999.]); Yoon et al. (1991[Yoon, U. C., Cho, S. J., Oh, J. H., Lee, J. G., Kang, K. T. & Mariano, P. S. (1991). Bull. Korean Chem. Soc. 12, 241-243.]); Zakai et al. (2010[Zakai, U. I., Bikzhanova, G. A., Staveness, D. & West, R. (2010). Appl. Organomet. Chem. In the press.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). Bond distances and angles were confirmed to be typical by a Mogul structural check (Bruno et al., 2002[Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.]).

[Scheme 1]

Experimental

Crystal data
  • C24H23NO2Si

  • Mr = 385.52

  • Monoclinic, C 2/c

  • a = 19.277 (3) Å

  • b = 13.238 (2) Å

  • c = 19.272 (3) Å

  • [beta] = 116.987 (6)°

  • V = 4382.5 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 300 K

  • 0.30 × 0.30 × 0.30 mm

Data collection
  • Bruker SMART X2S diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, GIS, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.964, Tmax = 0.964

  • 15551 measured reflections

  • 4470 independent reflections

  • 2693 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.175

  • S = 1.02

  • 4470 reflections

  • 254 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O2i 0.93 2.63 3.366 (4) 137
C14-H14A...O1ii 0.97 2.63 3.582 (3) 169
C19-H19...O2iii 0.93 2.51 3.310 (3) 144
C22-H22...O1iv 0.93 2.32 3.200 (3) 157
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 and GIS (Bruker, 2009[Bruker (2009). APEX2, GIS, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, GIS, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL, OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and FCF_filter (Guzei, 2007[Guzei, I. A. (2007). In-house Crystallographic Programs: FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, modiCIFer (Guzei, 2007[Guzei, I. A. (2007). In-house Crystallographic Programs: FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2024 ).


Acknowledgements

We thank Dr N. J. Hill (UW-Madison) for acquiring the data and Professor R. West (UW-Madison) for his support. We gratefully acknowledge Bruker sponsorship of this publication and also acknowledge grants NIH 1 S10 RRO 8389-01 and NSF CHE-9629688 for providing NMR spectrometers, and grant NSF CHE-9304546 for providing the mass spectrometer for this work.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bains, W. & Tacke, R. (2003). Curr. Opin. Drug Discov. Devel. 6, 526-543.  [PubMed] [ChemPort]
Bruker (2009). APEX2, GIS, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.  [ISI] [CrossRef] [details]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Gately, S. & West, R. (2007). Drug Dev. Res. 68, 156-163.  [ISI] [CrossRef] [ChemPort]
Guzei, I. A. (2007). In-house Crystallographic Programs: FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.
Guzei, I. A., Spencer, L. C. & Zakai, U. I. (2010a). Acta Cryst. E66, o219-o220.  [CrossRef] [details]
Guzei, I. A., Spencer, L. C. & Zakai, U. I. (2010b). Acta Cryst. E66, o223-o224.  [CrossRef] [details]
Lee, Y. J., Ling, R., Mariano, P. S., Yoon, U. C., Kim, D. U. & Oh, S. W. (1996). J. Org. Chem. 61, 3304-3314.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tsuge, O., Tanaka, J. & Kanemasa, S. (1985). Bull. Chem. Soc. Jpn, 58, 1991-1999.  [CrossRef] [ChemPort] [ISI]
Westrip, S. P. (2010). publCIF. In preparation.
Yoon, U. C., Cho, S. J., Oh, J. H., Lee, J. G., Kang, K. T. & Mariano, P. S. (1991). Bull. Korean Chem. Soc. 12, 241-243.  [ChemPort]
Zakai, U. I., Bikzhanova, G. A., Staveness, D. & West, R. (2010). Appl. Organomet. Chem. In the press.


Acta Cryst (2010). E66, o221-o222   [ doi:10.1107/S1600536809054117 ]

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